We caught up with the brilliant and insightful Michael Hollingsworth a few weeks ago and have shared our conversation below.
Alright, Michael thanks for taking the time to share your stories and insights with us today. What was the most important lesson/experience you had in a job that has helped you as a business owner?
Before moving to Illinois, I was an active duty serviceman in the United States Army. My positions in the military required me to learn how to spot deficiencies, how to work under pressure, how to pay attention to detail, and just how to be a leader in general.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
For this write-up, I want to focus on my clothing brand “SOBO,” which stands for “Stand Out, Be Original.” SOBO started in early 2020 with myself and a group of my closest childhood friends. We all grew up obsessed with fashion and what creative marketing ideas our favorite brands would come up with. Once my art career began gaining momentum last year, we all decided that it was the perfect time to put all of our ideas to work and to drop our first clothing collection. We still consider ourselves a relatively small brand, putting our main focus on quality of goods and a positive representation of our hometown, Gary, Indiana.
Our most recent Spring collection was sold during Spring Break at Navy Pier Chicago, one of the world’s most well known piers, and a Chicago landmark.

Do you have any insights you can share related to maintaining high team morale?
Just remember that there are fluctuations with life. Things aren’t always going to be good, and things aren’t always going to be bad. It’s understanding that balance that I think helps with team management and maintaining a high morale.
We’d love to hear your thoughts about selling platforms like Amazon/Etsy vs selling on your own site.
We currently sell our merchandise on our own website, powered by Shopify. We enjoy the ease of access that Shopify provides, along with the NFT integration that the platform allows.
Contact Info:
- Website: soboworkshop.com
- Instagram: @soboclothing.co
- Twitter: @soboclothingco
Image Credits
Navy Pier images courtesy of Navy Pier Chicago (Paris Williams)

